Iodine → 2,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

HRID 373549

Reaktionsgleichung

Reaktionsgleichung von HRID 373549
Br[C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.II.[O:15]1CC[CH2:17][CH2:16]1>BrCCBr>[CH3:17][CH:16]([C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1)[OH:15]

Komponenten

5

Edukt 3

HCID 807IodineHCID 8028TetrahydrofuranHCID 199355348-Bromo-2,3,4,5-tetrahydrobenzo[b]oxepine

Produkt 1

HCID 199354272,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 78391,2-DibromoethaneKatalysator

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

7.3 g of 8-bromo-2,3,4,5-tetrahydro-1-benzoxepine in 30 ml of absolute tetrahydrofuran were added under argon to 930 mg shavings and a granule of iodine. The reaction was intitiated by the addition of a few drops of 1,2-dibromoethane and has finished after 2 hours. Thereafter, the reaction mixture was cooled to -10° C. and excess acetaldehyde was distilled into the reaction vessel. After 10 minutes, the mixture was hydrolyzed with saturated sodium bicarbonate (NaHCO3) solution, extracted with ether, washed with water, dried and evaporated to dryness. Chromatography on silica gel (petroleum ether/ethyl acetate 3:1) yielded 4.93 g of 2,3,4,5-tetrahydro-α-methyl-1-benzoxepine-8-methanol as a colorless oil.

Aufarbeitung

  1. distillationexcess acetaldehyde was distilled into the reaction vessel
  2. waitAfter 10 minutes
  3. extractionextracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c8c67de915d2404f9289478b5992c195
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164387

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